Weston, MA Homes

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  /39

  $1,885,000

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft

  14 October Ln, Weston, MA 02493

  Situated at 14 October Ln in Weston, MA, this single-family residence, constructed in 1960, offers 3485 square feet of meticulously maintained living space. This attractive property, in great condition, presents an exceptional opportunity for refined living within a distinguished community. The kitchen serves as a central gathering space, distinguished by its high ceiling, elegant stone counters,

  Steven In RE/MAX Culture

  14 October Ln, Weston, MA 02493
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  /13

  $1,030,000 Sold Dec 18, 2025

  6 Overlook Dr, Weston, MA 02493

  • 3 Beds
  • 1.5 Baths
  • 1,390 Sq Ft
  • Built 1948

  Last Sold Summary

  • 12% Below List Price
  • $741/SF
  • 117 Days On Market

  Current Estimated Value $1,440,006

  Last Listing Agent Jaime Venezia Real Estate Pros Inc.

  6 Overlook Dr, Weston, MA 02493
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  /34

  Est $2,952,767 Not Listed For Sale

  40 Chiltern Rd, Weston, MA 02493

  • 5 Beds
  • 7 Baths
  • 5,680 Sq Ft
  • Built 1953

  40 Chiltern Rd, Weston, MA 02493

  Last Sold Summary

  • 8% Above List Price
  • $482/SF
  • 27 Days On Market

  • Last Sold Price $2,740,000
  • Nov 15, 2024

  Last Listing Agent The Shulkin Wilk Group Compass
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  /39

  $7,590,000

  • 6 Beds
  • 7.5 Baths
  • 8,421 Sq Ft

  286 Country Dr, Weston, MA 02493

  This custom-built modern estate sits prominently on a 1.42-acre corner lot and pairs striking architectural design with uncompromising craftsmanship across ~8,421 SF and 3 curated levels. A dramatic entry welcomes you into a soaring foyer anchored by a sculptural staircase and statement lighting, setting the tone for the home’s sophisticated aesthetic. Expansive floor-to-ceiling glass floods each

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  286 Country Dr, Weston, MA 02493
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  /37

  $3,500,000 Sold Mar 30, 2026

  10 Audubon Rd, Weston, MA 02493

  • 5 Beds
  • 5.5 Baths
  • 5,409 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $647/SF
  • 16 Days On Market

  Current Estimated Value $3,728,186

  Last Listing Agent Mizner+ Montero Gibson Sotheby's International Realty

  10 Audubon Rd, Weston, MA 02493
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  /37

  Est $2,386,605 Not Listed For Sale

  21 Gail Rd, Weston, MA 02493

  • 4 Beds
  • 3.5 Baths
  • 4,615 Sq Ft
  • Built 1956

  21 Gail Rd, Weston, MA 02493

  Last Sold Summary

  • 8% Above List Price
  • $481/SF
  • 5 Days On Market

  • Last Sold Price $2,220,000
  • Jul 10, 2024

  Last Listing Agent Alpha Group Compass
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  /42

  $1,890,000

  • 3 Beds
  • 6 Baths
  • 3,345 Sq Ft

  40 Hobbs Brook Rd, Weston, MA 02493

  Introducing a sophisticated contemporary home, perched on a hill with exceptional privacy, serene surroundings and a true connection to nature. The versatile and open design integrates the inside with the zen-like landscape for an elevated entertainment experience. The well-equipped kitchen and large dining area are complemented by multiple sitting areas. Three well-appointed bedrooms, including

  Mizner+ Montero Gibson Sotheby's International Realty

  40 Hobbs Brook Rd, Weston, MA 02493
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  /40

  $1,715,000 Sold Nov 06, 2025

  71 Silver Hill Rd, Weston, MA 02493

  • 3 Beds
  • 2.5 Baths
  • 3,108 Sq Ft
  • Built 1941

  Last Sold Summary

  • 4% Below List Price
  • $552/SF
  • 40 Days On Market

  Current Estimated Value $1,690,814

  Last Listing Agent Jeffrey Holden Coldwell Banker Realty - Newton

  71 Silver Hill Rd, Weston, MA 02493
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  /21

  Est $3,470,815 Not Listed For Sale

  25 Byron Rd, Weston, MA 02493

  • 5 Beds
  • 4.5 Baths
  • 5,802 Sq Ft
  • Built 2016

  25 Byron Rd, Weston, MA 02493

  Last Sold Summary

  • 13% Above List Price
  • $531/SF
  • 20 Days On Market

  • Last Sold Price $3,080,000
  • Jun 30, 2023

  Last Listing Agent The Shulkin Wilk Group Compass
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  /42

  $2,650,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 5,271 Sq Ft

  53 Stonehedge Rd, Lincoln, MA 01773

  Perched on a private hilltop at the end of a tranquil cul-de-sac, this custom mid-century modern Deck House sits on 3+ stunning acres with a heated pool, professionally landscaped grounds, bluestone terrace, pergola, tennis court, and direct access to 100+ acres of conservation land. Inside, soaring ceilings, where floor-to-ceiling windows flood the home with light seamlessly blends indoor and

  Terry Perlmutter Barrett Sotheby's International Realty

  53 Stonehedge Rd, Lincoln, MA 01773
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  /42

  $5,450,000 Sold Jul 08, 2025

  26 Spruce Hill Rd, Weston, MA 02493

  • 6 Beds
  • 6.5 Baths
  • 8,495 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $642/SF
  • 95 Days On Market

  Current Estimated Value $5,326,946

  Last Listing Agent Chaplin Partners Compass

  26 Spruce Hill Rd, Weston, MA 02493
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  /37

  Est $1,546,990 Not Listed For Sale

  29 Woodchester Dr, Weston, MA 02493

  • 3 Beds
  • 2 Baths
  • 1,828 Sq Ft
  • Built 1953

  29 Woodchester Dr, Weston, MA 02493

  Last Sold Summary

  • 3% Above List Price
  • $821/SF
  • 7 Days On Market

  • Last Sold Price $1,500,000
  • Jun 23, 2023

  Last Listing Agent Jane Meterparel and Brian Marvelley Churchill Properties
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  /33

  $3,625,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,985 Sq Ft

  1 Pine Summit Cir, Weston, MA 02493

  Curated style and luxury to be found at 1 Pine Summit Circle. This spacious, stand alone condominium features an open floor plan, fabulous great room, private first floor primary suite with luxurious bath, study, and two walk in closets. The great room opens to a true cook's kitchen and is the heart of the home. A gas fireplace with marble surround, generous breakfast area, access to a private

  Leeann Yolin Coldwell Banker Realty - Weston

  1 Pine Summit Cir, Weston, MA 02493
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  /41

  $6,600,000 Sold Mar 31, 2026

  180 Highland St, Weston, MA 02493

  • 5 Beds
  • 7.5 Baths
  • 11,300 Sq Ft
  • Built 2006

  Last Sold Summary

  • 12% Below List Price
  • $584/SF
  • 104 Days On Market

  Current Estimated Value $7,586,846

  Last Listing Agent rosemary mccready Compass

  180 Highland St, Weston, MA 02493
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  /35

  Est $2,730,447 Not Listed For Sale

  4 Pond Brook Cir, Weston, MA 02493

  • 5 Beds
  • 4 Baths
  • 4,494 Sq Ft
  • Built 1953

  4 Pond Brook Cir, Weston, MA 02493

  Last Sold Summary

  • 1% Above List Price
  • $601/SF
  • 41 Days On Market

  • Last Sold Price $2,700,000
  • Aug 02, 2024

  Last Listing Agent Christman Johnsson Group Hammond Residential Real Estate
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  /31

  $7,295,000

  • 6 Beds
  • 7.5 Baths
  • 8,773 Sq Ft

  5 Deer Path Ln, Weston, MA 02493

  This newly-constructed, Contemporary offers the pinnacle of luxury living on Weston’s coveted Southside. The dramatic, 2-story foyer flows seamlessly into both formal & informal spaces. The dining/living room is optimal for family gatherings & entertaining, and the custom kitchen w/an exceptional quartz island, high-end appliances & wet bar adjoins a generous eat-in area & fireplaced family room

  Beyond Boston Properties Group Compass

  5 Deer Path Ln, Weston, MA 02493
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  /15

  $855,000 Sold Mar 19, 2026

  19 Jericho Rd, Weston, MA 02493

  • 2 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Above List Price
  • $629/SF
  • 8 Days On Market

  Current Estimated Value $782,566

  Last Listing Agent Peter Hill MGS Group Real Estate LTD - Wellesley

  19 Jericho Rd, Weston, MA 02493
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  Est $2,228,505 Not Listed For Sale

  528 Glen Rd, Weston, MA 02493

  • 5 Beds
  • 3 Baths
  • 3,234 Sq Ft
  • Built 1946

  528 Glen Rd, Weston, MA 02493

  Last Sold Summary

  • 19% Above List Price
  • $580/SF
  • 4 Days On Market

  • Last Sold Price $1,876,000
  • Jun 23, 2023

  Last Listing Agent rosemary mccready Compass
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  /15

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,395 Sq Ft

  416 Conant Rd, Weston, MA 02493

  Built in 2022 with a blend on modern and traditional. Excellent open floorplan with 4 bedrooms, each with ensuite bathroom. 9' ceilings with large windows on the first and second floors make this smaller house spacious. Large deck that overlooks a private backyard. The home is heated with a 95% efficient Viessmann gas boiler, and has foam insulation throughout. Finished walk out basement and

  Derek Greene The Greene Realty Group

  416 Conant Rd, Weston, MA 02493
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  /42

  $5,420,000 Sold Jun 27, 2025

  57 Westcliff Rd, Weston, MA 02493

  • 6 Beds
  • 8 Baths
  • 8,005 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $677/SF
  • 60 Days On Market

  Current Estimated Value $5,153,956

  Last Listing Agent Melissa Dailey Coldwell Banker Realty - Wellesley

  57 Westcliff Rd, Weston, MA 02493
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  /41

  Est $2,790,832 Not Listed For Sale

  8 Shady Hill Rd, Weston, MA 02493

  • 5 Beds
  • 6 Baths
  • 6,152 Sq Ft
  • Built 1953

  8 Shady Hill Rd, Weston, MA 02493

  Last Sold Summary

  • 3% Above List Price
  • $441/SF
  • 63 Days On Market

  • Last Sold Price $2,710,000
  • Jan 24, 2025

  Last Listing Agent Mizner+ Montero Gibson Sotheby's International Realty
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  /19

  $7,550,000

  • 6 Beds
  • 9 Baths
  • 8,863 Sq Ft

  132 Country Dr, Weston, MA 02493

  Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen

  Sheryl Simon Gibson Sotheby's International Realty

  132 Country Dr, Weston, MA 02493
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  /38

  $2,700,000 Sold May 06, 2026

  126 Newton St, Weston, MA 02493

  • 4 Beds
  • 3.5 Baths
  • 3,152 Sq Ft
  • Built 1872

  Last Sold Summary

  • 13% Above List Price
  • $857/SF
  • 3 Days On Market

  Current Estimated Value $2,541,534

  Last Listing Agent Denise Mosher Coldwell Banker Realty - Weston

  126 Newton St, Weston, MA 02493
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  /35

  Est $4,520,562 Not Listed For Sale

  90 Sylvan Ln, Weston, MA 02493

  • 5 Beds
  • 8 Baths
  • 6,027 Sq Ft
  • Built 2008

  90 Sylvan Ln, Weston, MA 02493

  Last Sold Summary

  • 10% Above List Price
  • $680/SF
  • 7 Days On Market

  • Last Sold Price $4,100,000
  • Aug 22, 2023

  Last Listing Agent Melissa Dailey Coldwell Banker Realty - Wellesley
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  /40

  $5,495,000

  • 5 Beds
  • 8 Baths
  • 9,200 Sq Ft

  300 Glen Rd, Weston, MA 02493

  Stunning shingle style 5 bedroom home on Weston's South side. Completely renovated kitchen & baths giving this home the ideal layout, style & convenient location. Light filled kitchen w/ large picture window overlooks the 2.68 acres plus abutting conservation land w/ trails. Huge center island & high end appliances w/ working fireplace in kitchen. Adjacent family room w/ coffered ceilings,

  Melissa Dailey Coldwell Banker Realty - Wellesley

  300 Glen Rd, Weston, MA 02493
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  /17

  $802,000 Sold Jun 30, 2025

  105 Jericho Rd Unit 105, Weston, MA 02493

  • 2 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Above List Price
  • $590/SF
  • 4 Days On Market

  Last Listing Agent Denise Mosher Coldwell Banker Realty - Weston

  105 Jericho Rd Unit 105, Weston, MA 02493
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  /41

  Est $3,789,285 Not Listed For Sale

  52 Sylvan Ln, Weston, MA 02493

  • 5 Beds
  • 5 Baths
  • 5,241 Sq Ft
  • Built 1972

  52 Sylvan Ln, Weston, MA 02493

  Last Sold Summary

  • 8% Above List Price
  • $667/SF
  • 3 Days On Market

  • Last Sold Price $3,495,000
  • Jul 28, 2023

  Last Listing Agent Tori MacDowell Gibson Sotheby's International Realty
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  /22

  $3,195,000

  • 4 Beds
  • 4.5 Baths
  • 5,438 Sq Ft

  183 Conant Rd, Weston, MA 02493

  Stunning custom new construction in a prime Weston location offering 5,500+ sqft of thoughtfully designed living space. This gorgeous home features a flexible open floor plan with option for a 1st-floor bedroom or office. The chef’s kitchen boasts premium appliances, gas cooktop, custom cabinetry, and a large center island perfect for entertaining. The 2nd level includes 3 spacious bedrooms, den

  Gabby Cefalo Coldwell Banker Realty - Wellesley

  183 Conant Rd, Weston, MA 02493
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  /34

  $2,895,000 Sold Feb 20, 2026

  3 Clifford Ln, Weston, MA 02493

  • 5 Beds
  • 6 Baths
  • 6,300 Sq Ft
  • Built 2025

  Last Sold Summary

  • 17% Below List Price
  • $460/SF
  • 307 Days On Market

  Current Estimated Value $2,976,500

  Last Listing Agent Gary Litchfield Mass. Real Estate Solutions, LLC

  3 Clifford Ln, Weston, MA 02493
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  /42

  Est $8,208,863 Not Listed For Sale

  24 Sylvan Ln, Weston, MA 02493

  • 6 Beds
  • 9 Baths
  • 10,100 Sq Ft
  • Built 2015

  24 Sylvan Ln, Weston, MA 02493

  Last Sold Summary

  • 3% Above List Price
  • $792/SF
  • 8 Days On Market

  • Last Sold Price $8,000,000
  • Jul 06, 2023

  Last Listing Agent Sheryl Simon Gibson Sotheby's International Realty
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  /42

  $1,397,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,554 Sq Ft

  43 Sherburn Cir, Weston, MA 02493

  Sited in a terrific South Side neighborhood and set way back off an idyllic residential street at the crest of a hill, you'll find this attractive home built in 1961. Highlighting the main level is the updated, bright kitchen with vaulted ceilings and 2 oversized skylights. There is plenty of room for your sit down breakfast table, and there is direct access outside to a lovely flagstone patio

  Edward Lyon Preservation Properties

  43 Sherburn Cir, Weston, MA 02493
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  /28

  $1,400,000 Sold Jan 23, 2026

  1 Aberdeen Rd, Weston, MA 02493

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft
  • Built 1933

  Last Sold Summary

  • 9% Below List Price
  • $622/SF
  • 56 Days On Market

  Current Estimated Value $1,409,271

  Last Listing Agent Paige Yates Coldwell Banker Realty - Weston

  1 Aberdeen Rd, Weston, MA 02493
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  /25

  Est $1,205,036 Not Listed For Sale

  2 Dickson Ln, Weston, MA 02493

  • 3 Beds
  • 3.5 Baths
  • 2,930 Sq Ft
  • Built 1996

  2 Dickson Ln, Weston, MA 02493

  Last Sold Summary

  • 8% Above List Price
  • $382/SF
  • 9 Days On Market

  • Last Sold Price $1,120,000
  • Aug 23, 2024

  Last Listing Agent Denise Mosher Coldwell Banker Realty - Weston
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  /42

  $5,999,000

  • 4 Beds
  • 7 Baths
  • 7,600 Sq Ft

  44 Meadowbrook Rd, Weston, MA 02493

  This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has

  Mizner+ Montero Gibson Sotheby's International Realty

  44 Meadowbrook Rd, Weston, MA 02493
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  /39

  $5,450,000 Sold Jan 15, 2026

  15 Whitney Tavern Rd, Weston, MA 02493

  • 6 Beds
  • 8 Baths
  • 7,501 Sq Ft
  • Built 2025

  Last Sold Summary

  • 16% Below List Price
  • $727/SF
  • 113 Days On Market

  Current Estimated Value $5,377,449

  Last Listing Agent Maggie Gold Seelig MGS Group Real Estate LTD

  15 Whitney Tavern Rd, Weston, MA 02493
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  /30

  Est $1,705,417 Not Listed For Sale

  181 Winter St, Weston, MA 02493

  • 5 Beds
  • 3.5 Baths
  • 3,034 Sq Ft
  • Built 1937

  181 Winter St, Weston, MA 02493

  Last Sold Summary

  • 7% Above List Price
  • $527/SF
  • 106 Days On Market

  • Last Sold Price $1,600,000
  • Mar 29, 2024

  Last Listing Agent Katya Malakhova William Raveis R. E. & Home Services
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  /27

  $1,675,000

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  37 School St, Weston, MA 02493

  Beautifully sited on over 2 private acres, this 8-room, 4-bed, 3-bath home offers comfort, charm, and room to grow. The spacious living room features a fireplace and hardwood floors, flowing into a formal dining room with two classic corner cabinets and a sun-filled kitchen with white cabinetry, stainless appliances, and center island. Two generous bedrooms and a full bath complete the first

  Denise Mosher Coldwell Banker Realty - Weston

  37 School St, Weston, MA 02493
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  /30

  $2,565,000 Sold Mar 31, 2026

  156 Cherry Brook Rd, Weston, MA 02493

  • 4 Beds
  • 4.5 Baths
  • 4,379 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $586/SF
  • 14 Days On Market

  Current Estimated Value $2,580,817

  Last Listing Agent Elizabeth Crampton Coldwell Banker Realty - Lexington

  156 Cherry Brook Rd, Weston, MA 02493
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  /38

  Est $2,646,891 Not Listed For Sale

  11 Beaver Rd, Weston, MA 02493

  • 4 Beds
  • 4 Baths
  • 3,580 Sq Ft
  • Built 1965

  11 Beaver Rd, Weston, MA 02493

  Last Sold Summary

  • 6% Above List Price
  • $698/SF
  • 126 Days On Market

  • Last Sold Price $2,500,000
  • Sep 10, 2024

  Last Listing Agent Christine Norcross William Raveis R.E. & Home Services
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  /38

  $4,795,000

  • 6 Beds
  • 7 Baths
  • 7,000 Sq Ft

  21 Westerly Rd, Weston, MA 02493

  1.38 acres of flat land in coveted Weston Estates! Stunning shingle and stone 6 bedroom Colonial. Extraordinary outdoor space featuring a pavilion with kitchen plus stone fireplace perfect for outdoor living and entertaining. Large kitchen with oversized island and seating area opens to double storeyed family room along with beautiful floor to ceiling stone fireplace, wet bar and incredible

  Melissa Dailey Coldwell Banker Realty - Wellesley

  21 Westerly Rd, Weston, MA 02493

Showing Results 121 - 160, Page 4 of 18